Potassium Fluoride → HCID 67197500, compound

Participants

Reaction Steps

A mixture of 3-(5-bromothiophen-2-yl-methyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 45-(3) (345 mg), 2-(tri-n-butylstannyl)pyridine (997 mg), copper(I) iodide (20 mg) and tetrakis(triphenylphosphine)-palladium(0) (63 mg) in toluene (10 ml) was refluxed for 3 hours under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and thereto was added a 10% aqueous potassium fluoride solution. The resultant mixture was stirred vigorously, and the insoluble materials were filtered off. The filtrate was separated, and the organic layer was washed with brine and dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate=90:10-50:50) to give 4-methyl-3-(5-(2-pyridyl)thiophen-2-yl-methyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole (122 mg) as a pale yellow solid. APCI-Mass m/Z 635 (M+H).

Provenance & Evidence